One On One with James Stapleton

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Hello, geeks, and welcome to the Social Geek Podcast, the most popular franchise podcast. I’m Jack Monson, your host and marketing Consigliere.

We’ve got another Franchise Thought Leadership Award winner joining me today for a one-on-one conversation. My guest is James Stapleton, Vice President of Franchise Development at Caring Transitions.

All right, today’s show is brought to you by Pilot, AnswerConnect, and before we get going, a quick note from Thunderly. Are your Frandev marketing agencies, content creators and PR teams really working together? Learn how Thunderly’s amplified integrated marketing can drive franchise development growth at thunderlymarketing.com.

James Stapleton is the VP of Franchise Development at Caring Transitions, and he’s one of this year’s Social Geek Franchise Thought Leadership Award winners, and I’m glad to have him on the podcast today. James, how are you?

I am awesome. Jack, thanks for having me. And thanks for the award, man. I mean, this franchise world is absolutely amazing. I cannot imagine doing anything else in my career besides being around these amazing people.

Well, I think that comes out in all of the content that you’re putting out there, LinkedIn posts and all of that kind of thing, because the voters spoke and you were one of the winners this year, and it definitely comes out in the things that you’re writing and saying every day. So you’re with Caring Transitions, and you’re also an advisor with a group called Strategic Franchising. Tell me about that structure. Is that like a platform of brands or what does that look like?

So, Strategic is our affiliate company. So there’s franchised concepts underneath the strategic portfolio, including Fresh Coat, True Blue, Pet Wants and the Growth Coach. So, you know, we kind of like work together. I work a lot with the CEO on different sales concepts for the other brands itself. When I came into Caring Transitions, there really wasn’t much structure, right? So I was able to come in and set a foundational structure of what kind of sale this is. I was professionally sales trained back in the day doing door-to-door insurance sales.

Oh, boy.

Someone’s door in the house, the old fashion way sitting in the kitchen table. So I understood how people think and people make decisions and, you know, to really navigate a process and take them on a journey, right? So I was able to put the structure in place that worked very well for us, that I’m able to help some of the other directors, some of the other VPs, so we can all work together and be collaborative on, you know, ways that can help them with their brands and, you know, move in their people forward.

So that’s got to be a little bit different than when you came into the industry, sort of focused on one brand versus now you’ve got a portfolio of opportunities for people. Is that one of the biggest differences you’ve seen in your time in franchising?

I, well, I mean, it’s more or less advice. You know, I’m an advisor. I’m not a boss in any way, shape or form to these people. It’s more or less like best practices.

Yeah. So you’re coaching more than bossing.

Yeah, exactly. I mean, I’m still 100% focused on Caring Transitions. That’s where I’m, you know, leading the charge and leading the team and driving to the results that we have. That is my main role. But, you know, to be able to drop in and be able to help with some of the processes or, you know, any way I can help any of the other brands. I mean, that’s the focus there.

You might as well have that advisor title because they’re going to call you anyway and ask for your help, right?

You know, it is kind of the guru in the mountain, you know, like, hey, something’s going on on this side. Okay, well, then check this person out or, yeah, let me show you the go-to person in the office, which, you know, it makes me feel good that, you know, I have an answer to be able to help people, you know, not just prospects coming through, but other brands and stuff like that, too.

Yeah, as I tell people all the time, I might not know the answer, but that doesn’t mean I’m not going to answer. So what else have you seen change in your time so far in franchising? And you’ve been technically in franchising now for seven to 10 years, something like that. Do I have that timeline?

I’ve been in sales for 30, but I’ve been in franchising for seven.

Got it.

You know, coming into this industry, not knowing like what to expect. I mean, I’ve dipped my toe in different sales organizations throughout the years, and all of them have their different way that people approach collaborative working together, or, you know, ways to be able to structure things that, you know, help people get to a solution itself. This, man, ever since I’ve been here, it’s more of a family environment. I think it’s old school to think like, this is mine and I’m not, you know, sharing any information or, you know, giving anything over. We’d all make so much more money if we all worked together.

Yeah.

So-

That’s kind of the definition of franchising.

Yeah, right, exactly. Like, why do it on your own? And me, not coming from franchising, you know, coming from this outside world, kind of forced me into this of, you know, sitting with people at lunch or going out for drinks and just talking and I’m a sponge. So for me, it’s all about being able to not share my knowledge of, you know, what I know, but like asking more questions, same way with the prospect, right? Asking more questions about like, how does this work? How do you guys do this? And what I found is we all take goal on the same journey. We all do kind of the same steps to get to the same result, right? Everybody does a territory check. Everybody does FTD review. Everybody does, you know, and their discovery calls. Everybody meets the team. But we all do it in a different way. And we all do it sometimes totally differently. Some people have really long processes. Some people have really short processes. So to be able to come into this world and, you know, not as the, as the expert and the guru, but, you know, more of like the student and hearing how people are doing things. I mean, like, oh, I like that.

Yeah.

And taking that and being able to put it in my own process and run with it. I mean, it all accumulated a couple of years ago when I was talking to the IFA about, I think I want to start a mastermind group for franchise development. Let’s find the movers and shakers in the industry. We should all be talking about what we do and how it works, right? So I started a group called Steel Sharpen Steel that has the movers and shakers across the franchisers. And we talk about Framdev. We’ve talked about KPIs. We’ve talked about Discovery Days. We just talked about trust in the process and how important that is. You know, I’m building this core group of people that, you know, if we need something, we’ve got that. They’re the first stop, right?

Yeah. Yeah, I think franchising is unique in that even people who technically are competitors are constantly sharing ideas and actually making each other better at what they do. I’ve been in some other industries too, and I have not seen that in many other industries.

No, you know, and so coming into it, you’re not sure like what to share, what to do. But you know, like the connection I’ve made with the people in this industry have been some of the most solid friends that I’ve made in years, you know. To go to an event and really be excited to see the people that are there, I think is a weird concept of most other industries, right? Because I mean, we have a friend or two, but I mean, I’m really looking forward to like, hey, who’s going to be at this event? Where are we going to do karaoke? What’s where we connecting? And then also like the successes you had, genuine people that celebrate with you. I mean, I love celebrating. And that’s one of my favorite things is somebody going, oh my god, I just had an amazing day. Oh my god, tell me all about it, right? But also, you’re at these events. I’ve had people pull me aside just randomly and been like, hey, I’m in a situation. Can I talk through with you? Oh my god, absolutely. Let’s sit over here and talk through whatever situation you’re going through. Like, I love all that kind of stuff, you know? It’s, I was just telling one of my new hires that I used to be part of the sales world. I was the top sales guy at every organization I’ve ever been in. And I stepped out of sales last year. So now I’m, you know, the leader of the brand and, you know, big picture ideas and everything else and letting the team, you know, and when you hand over something like that to somebody else to take care of it, you think, oh my God, is this going to fall apart or not? But man, when it doesn’t fall apart and it excels from where you left off on it, and when you see your team hitting goals and breaking records and making money, man, that is a bigger high than any other sale I’ve ever made.

Oh yeah, because you’re part of it along with a bigger group. It isn’t just your individual track record.

Yeah.

Yeah.

It’s not like, okay, what do we need? I’m going to, you know, big Jim’s going to come in on the white horse and save the day. You know, when you don’t have that option and you got to rely on the people on your team and the trust you build and the, and it also lets you know your process works, right?

Yeah.

As you set up, they’re following that same process. And guess what? They’re making sales. So anybody that I bring into this organization from then on, I can tell them with full confidence, just like a franchise system. You do these steps, you can be successful.

Yeah.

Yeah.

It really is like a franchise system and putting together a proven program that you must follow and we will all be successful. So yeah, I love that comparison.

The validation is talk to you, talk to the other directors on the team, right? And the beauty of it too is the way this process is set up is they don’t have to sound like me. I don’t want anybody sounding like me. Everybody’s personality is different. I tell them right off the bat, like, here’s the steps, but I want you to put your own personality. I want you to be able to, you know, put your own knowledge and experience. And, you know, there’s a reason you’re on this team right now is because you are a sales rock star. So I want you to be able to have your own personality, but framing around what the framework is here, right? And everybody on my team goes through kind of the same steps, but they all do it 100% different. Yeah, that really shows that it’s malleable, right? And it can work no matter who is in front of it. To be able to have people, you know, buy a business is going to change your life.

Yeah, we, I love that idea. We were talking a little baseball before we started recording today. And it’s like every baseball team has nine guys who swing the bat a little bit differently. And you’re not going to have two guys swinging the bat exactly the same. So, but they’re all good enough to be in the major leagues. Yeah, so, yeah, so yeah, we can’t, don’t just imitate somebody else because you’re probably going to strike out.

And that’s how you set the people up for failure and that’s how they get frustrated. And that’s, you know, like I said, I was the top sales guy in all these different organizations. And, you know, if somebody came in and said, oh, you can’t tell any corny jokes. You gotta, you gotta be very robotic in your presentation.

You wouldn’t have anything to say. Oh, my God.

There was one that like, there was a whole, everything was scripted. The jokes were scripted, right?

Oh, no.

You know, but I was able to say, okay, if that’s your process, then fine. I’ll be able to do it like the back of my hand. And I was able to put my own personality into it. So when I was delivering those scripted jokes, I was delivering that joke. So Megan’s here, I was hitting home because that’s what I had to do.

Yeah. I hope there’s some video of that somewhere that we can unearth.

God, I hope not. No. This would probably be four cell phones if I were in the room.

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I think it’s a mixture of both. I think nothing’s static. And if you think that your process is solid and there’s no change that can be made, then I think you’re in trouble. I’ve got a 200-page playbook that I put together for the sales side of when a new person comes through, that is a literally written workbook. I want them to take pen to paper and write out their ideas because I think there’s something magic that happens between your hand and your brain when you’re physically have to write it out. But I also think that there’s this new wave of… AI excites me at this point. When I first heard about it, I’m thinking Terminator 2 and Judgment Day, right? Oh, no.

What’s going to happen to me?

Here it comes, but I think it’s either you can fear it or you can dive into it. I’m at the dive into it part myself, but here’s the problem is I’ve been doing AI sessions and learning more about it, but I feel like I’m a caveman with fire, right? Like I got this amazing thing and I just don’t know how to use it. So the more I learn about it, it just my head explodes every time. It’s like I just found out about agents the other day that they can go off and do these little test. I’m like, wait, what? So I think the more that I can understand it, more we can get into it, and the more that this develops, a lot of these processes that we’re doing that are so manual that are taking so much time for my team to get through, are going to be streamlined, and it’s going to be much easier for them to focus on the person in front of them, the journey they have, and not have to worry about putting in the notes and doing all the manual things and doing all these steps that are just taking time away from that relationship they can be building.

Yeah. If AI can take some tasks away from you, why were you doing those tasks in the first place? So especially if you’re talking about, you know, I see this happening with the Fran Dev folks out there becoming much more of an executive level profession, having much higher level conversations than just back in the old days. And by the old days, I mean, five years ago. You know, people just, you know, dialing and smiling and grinding away. Like, we don’t need to do that anymore.

And that’s still part of the job that is the worst, is trying to get a whole new people, right? It’s like, man, just give me something I can talk to. Let’s, this would be absolutely amazing. This would be magic if we can be able to figure out, you know, what’s your problem? Let’s get a solution and get people through, right?

Yeah, good way to describe AI. Just consider it magic, right? What do you want it to do?

Let’s get it, caveman with fire. I got this amazing thing in front of me. I just don’t know what to do with it, right?

I don’t know how it was created, but I know how I’m going to use it. Let me ask you the same question about senior care. You guys just seems like you’re on fire right now, not only with your brand, but also lots of brands in the space are just having a tremendous couple of years. Obviously, there’s an aging population and things like that may be contributing, but where do you see senior care going over the next few years?

You know, when it comes to, I mean, in franchising, if you’re really looking for a passion brand, it falls into three things. It’s either seniors, pets, or kids, right? Those are the three things that most people fall into.

The three things I’ll spend money on, yeah.

Yes, exactly. No matter what. Either you want to spend money on it or you have to spend money on it, right? I mean, being in the senior industry, it’s a hot industry, you know, because I mean, we are at the points in history where we got more people turning 65 than ever before, right?

Yeah.

And with what we and everybody really in this industry deal with, we’re dealing with the two things we can’t control in this world, which is getting old and getting sick. That’s going to happen no matter what happens in the world.

Yeah.

So there’s always going to have to be a solution for this. Now, us being in this senior industry, but most people think when they hear Caring Transitions, they stop me. They’re like, Oh, I know about in-home health care. Oh, I know about senior placement. I know about driving grandma around for groceries. Like we don’t do any of that. You know, for us, it’s we are the leading provider of senior relocation and the resale of household goods. So what we do is we find seniors looking at downsize and into a smaller apartment, sister living facility, maybe in with the kids. We’ll go into the house, box mom up, move her over, resettle her in the new place, then go back into the house, do an estate sale or an online sale, and then clean it out so it could be resold faster. You know, really what we’re, what our owners are selling is time.

Yeah.

You know, I’m not sure if you’ve ever been part of a downsize for a family member before.

Oh yeah, yeah. And I think too where the way people live, especially in the United States these days, is no one lives five blocks away from mom or grandma. Right. They’re all, it seems like everybody’s 2000 miles away from the people that they need to take care of suddenly. So to have that sort of local, it’s time, but it’s also convenience. And for me to not have to fly across the country to take care of this myself, like what you guys do, that’s amazing, especially in this day and age.

You said it, it’s suddenly.

Yeah.

Nobody plans for something like this to happen. If we all knew the day something was gonna happen to us, we’d make a plan the day before.

Right. Yeah.

So for us, it’s all, the people that are calling us, they’re already neck deep in the situation, looking for a solution. They’re Googling at two in the morning, like, what do I do with mom? And trying to find a solution to this. So, and we’ve found that it takes the average American family nine months ago from start to finish when they’re faced with something like this. When something like that happens and mom is in this new strange reality that now is her every day, is very bitter about leaving her home that she’s been in for 30, 40, 50 years, raise the kids, have the memories. Now she’s kind of this recluse in this facility, living out of boxes, because the kids can’t be there. They got to clean the house up.

Yeah. Yeah.

So something that will take them months to do will take us a week or two. And it gives families time back to help mom settle in this new strange reality. So we coined a term called day one living. So in other words, what does that day one look like for a senior walking into this new strange reality that is now their every day? Are they walking in and there’s boxes and there’s months worth of stuff and the kids can’t be there? And they come this kind of hermit in the school apartment? Or can they walk in, everything is set up, pictures are hung, entertainment center, their favorite chairs on the same side, their dishes are put away, beds put together, clothes are put away. And from day one, they can sit on the couch, have a cup of coffee, the kids can be there and say, mom, let’s go take a look at what activities are going on. Hey, let’s meet your neighbors next door and help them settle into this new everyday to get the care that they need. That’s what Caring Transitions is, more than the stuff itself.

Yeah, great concept, helping them settle into the future. That’s great work, love it right there. James, if someone would like to have a conversation with you about the industry, about some of the things that you’re doing and maybe what the opportunities are out there, where can we send them?

Yeah, my email address is probably best.

Okay.

It is the letter J Stapleton, S-T-A-P-L-E-T-O-N, at caringtransitions.com. But if anybody is interested, definitely connect with me on LinkedIn. I’m very active on LinkedIn.

Obviously, as a Thought Leadership Award winner. Yes, you are.

Yeah, so, but I mean, I’m constantly sharing different tips. I’m constantly sharing information on Caring Transitions. I’m doing a series right now that is called Lessons for My Son, that gives different life lessons that I’ve learned from teachers and mentors that I’m like passing down to him.

Oh, cool. And you’re doing that on LinkedIn? Yep.

I’m up to 38 right now. 38 lessons that are on there. So it is really a way to pay it forward. You know, it’s the stuff that I wish that, you know, my parents would have, you know, that have given me or would give me more. Yeah.

Yeah.

Yeah.

Very good. Well, we will follow along on LinkedIn as well. Thank you so much for being here today. Congratulations once again on being named one of the Thought Leadership Award winners in franchising for 2026. And I’m sure we will see you at a big franchising event down the road soon.

I’m sure you will. All right. Thanks, Jack. I appreciate it.

Thanks to James Stapleton of Caring Transitions for joining me today. More One On One shows with more Franchise Thought Leadership Award winners are coming up. Thanks also to our sponsors, Pilot, AnswerConnect and Thunderly. And thanks to you for listening, telling a friend about us, and staying connected on the Social Geek Radio Network.